Sulfuric Acid → Urea, 1,1-bis(2-hydroxyethyl)-

HRID 2301208Notes

Reaction equation

HRID 2301208 reaction equation
[NH:1]([CH2:5][CH2:6][OH:7])[CH2:2][CH2:3][OH:4].S(=O)(=O)(O)O.[O-:13][C:14]#[N:15].[K+]>O>[OH:4][CH2:3][CH2:2][N:1]([CH2:5][CH2:6][OH:7])[C:14]([NH2:15])=[O:13]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8113DiethanolamineHCID 11378442Potassium cyanate

Product 1

HCID 98687Urea, 1,1-bis(2-hydroxyethyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

212.4 g diethanolamine in 212.4 g of water was neutralized with 101.85 g concentrated sulfuric acid to a pH of 4. A solution of 168.99 g potassium cyanate in 260 g of water was then added and the mixture was heated to 90° C. for 3 hours. After cooling to ambient temperature, potassium sulfate precipitated and was filtered out. The filter cake was washed with 425 g of hot ethanol. The recovered ethanol was then added to the contents of the filtrate, causing the filtrate to become cloudy. The white precipitate was removed by filtration and then the ethanol was removed by distillation to give a viscous liquid solution of N,N-bis(2-hydroxyethyl)urea. The product similarly could be obtained using other acids to neutralize the amine, e.g. sulfuric acid. Also, other cyanate salts could be used, e.g. sodium cyanate.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. custompotassium sulfate precipitated
  3. filtrationwas filtered out
  4. washThe filter cake was washed with 425 g of hot ethanol
  5. additionThe recovered ethanol was then added to the contents of the filtrate
  6. customThe white precipitate was removed by filtration
  7. customthe ethanol was removed by distillation

Sources & evidence

ORD record
ord-2c443053f06c4f9f99f69b8f2bcdd1b6
Source dataset
uspto-grants-2002_12
Patent number
US06500212B1

Reaction notes

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